Top Tech Jobs & Startup Jobs in Chicago, IL

Lead strategy and execution for end-to-end client booking across web and mobile, owning discovery, booking flows, checkout, confirmations, cancellations, and rebooking. Drive conversion, rebooking, and retention via data, experimentation, and AI; partner with Engineering, Design, Marketing, and Data to deliver scalable, high-quality B2C experiences and measurable business outcomes.

Lead technical vision and execution for SQUIRE, managing global engineering teams to deliver scalable, secure consumer-facing products, modernize legacy systems, and integrate generative AI to improve velocity and quality.

Lead and build SQUIRE's Product Marketing function: define positioning and category narrative, run product launches and pricing/packaging, enable sales with messaging and playbooks, translate customer and AI insights into GTM strategy, and partner cross-functionally to drive conversion, revenue, and adoption.

Lead strategy for SQUIRE's embedded payments platform, managing merchant and customer experiences while ensuring compliance and scalability.

The Customer Experience Specialist focuses on reducing customer churn by engaging with customers and providing consultative guidance on product usage. Responsibilities include handling cancellation requests, upselling, delivering training sessions, and collaborating with various teams to enhance customer satisfaction.